


Time for a Wedding!

by ChelseaStark_x



Series: Tumblr Prompts [7]
Category: Supernatural
Genre: Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Dean Winchester/Female Reader, F/M, Fluff, Gen, Happy Dean Winchester, Happy Sam Winchester, Jessica Moore Lives, Modern Era, Pep Talk, Reader-Insert, Reader-Interactive, Sam Winchester gets to be happy, Sam Winchester to the Rescue, Time For A Wedding
Language: English
Status: Completed
Published: 2019-07-31
Updated: 2019-07-31
Packaged: 2020-07-27 22:53:46
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,567
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20053861
Author URL: https://archiveofourown.org/users/ChelseaStark_x/pseuds/ChelseaStark_x
Summary: Prompt 60 with Dean Winchester x Reader please!60 - “I crashed your family member’s wedding for the free food but hi there”Reader crashes Sam Winchester's wedding party for the free food and ends up having a good time.





	Time for a Wedding!

**Author's Note:**

> Leave me a request in the comments of send me an ask on Tumblr!
> 
> https://multi-fandom-imagines-x.tumblr.com/post/186361507131/100-prompts-requests-open

  
You were staying in a hotel when you saw that a wedding party was being held in one of the party rooms. You raised your eyebrow as an idea formed in your head, you knew you had a fancy-ish dress you could throw on and blend in with the guests. It looked like there was enough people in there that you could pass as a distant friend of the family. A grin spread on your face when you saw the food that had been left on the table, who were you to pass up free food? Quickly, you headed back to your hotel room, slipping into something a little nicer than the hoodie-leggings combo you were rocking before adding a bit of makeup and heading back downstairs. It was easy enough to sneak into the room and over to the buffet table, grabbing a plate and going to town, helping yourself to the food.

“Best thing about a wedding, huh? The food.” Someone said to you, you turned to look at him. The man was definitely taller than you, looking insanely handsome in his fitted suit.

“Very true.” You laughed, biting down on a sandwich as you turned to face the sea of people who were eating, dancing, laughing, generally just having a good time. Your eyes landed on what was obviously the bride and groom, the groom was bent down, gently kissing his new bride though you could see the kiss was cut off quickly as he was smiling too wide.

“How’d you know the happy couple then?” He asked you with a grin as he too watched the couple. You paused for a second, panicking and cursing yourself for not creating a decent backstory before hand. You cleared your throat before answering him.

“Oh, I’m an old family friend of the groom. What about you?” You prayed to anyone who was listening that he bought your story. The stranger turned to face you, brow raised and a smirk playing on his lips as he took in your appearance.

“Family friend, huh? I’m the groom’s brother and I gotta say pretty face like yours, I think I’d remember you.” The smile fell from your face as you realised you had been caught, there was a 50/50 chance of getting caught out but the brother of all people, your luck really was bad.

“Ok, Ok, I crashed your family member’s wedding for the free food but hi there”  
You were thoroughly surprised when he laughed at you instead of immediately kicking you out, your eyebrow raised questioningly as he just leaned back against the table, continuing with eating his food.

“Gotta say, I’m pretty surprised I’ve never done that before. I mean, he has pie at this thing, why wouldn’t you crash the party?” He was still laughing as spoke, causing you to relax a bit and carry on working on your plate of food.

“So, I can stay?” You asked him with a sweet smile on your face, he chuckled again.

“Yeah, sure thing. But you gotta know the basic facts. The groom’s name is Sam Winchester, the bride is Jessica Moore. They’ve been together for so long, high school sweethearts. Sammy’s head over heels for the girl. Anyway, that man over there,” he said, pointing at another tall man, head shaved and a greying beard, “is John Winchester, our dad, and the man next to him is Uncle Bobby, practically a dad to us as well though.” He continued pointing out people you should know, telling you a bit more about his brother and Jessica as he did.

“Great, so I know practically the whole family, but I still don’t know your name.” You smiled as his eyes widened.

“Oh yeah, I’m Dean Winchester and you are?” You introduced yourself to him and he grinned. Quickly, he grabbed two plates and cut two slices of pie, setting them down before handing you one and dragging you over to where most of the family had gathered. Sam was the first to notice the two of you, excusing himself from the conversation he was having with, you wanted to say Jessica’s dad but honestly weren’t 100% sure.

“Dean, hey! Whose’s this?” He asked as he smiled at you.

“This is Y/F/N Y/L/N. She’s a friend of mine and I knew she was in town, thought I’d invite her to the party.”

“Oh well hey, it’s nice to meet you.” He told you, offering you a hand to shake which you did.

“You too. Congratulations!” He thanked you with a grin, you could see his eyes were glazed over, happiness and disbelief that he had married his longtime girlfriend. He looked like he knew he was the luckiest man in the world. You were introduced to Jessica before Dean introduced you to his father and Bobby.

After you had been acquainted with everybody, Dean led you to a table that was free and you spent hours trading stories back and forth, telling each other your hobbies, likes and dislikes, jobs, goals, favourite music and movies, pretty much anything that came to mind. There was never a lull in the conversation, you both were enjoying the others company. A night that had started off pretty crappy for you had been transformed so quickly. The intention you had when you came in here was free food to eat whilst you moped around, but you ended up truly enjoying yourself, forgetting about the bad things that had happened that day.

“Care to dance?” Dean asked as he stood, offering you his arm.

“Oh no, no. I don’t dance.” You told him with a slight blush.

“Sure you do.” He replied with a cheeky grin, grabbing your hand and pulling you to the dance floor just as a slow song started. You rested your arms around him, Dean does the same to you as he started moving. You swayed gently and moved your feet as he directed, resting your head against his shoulder as you let yourself relax into the dance.

“See you do dance.” He laughed, causing you to groan, but smile up at him.

You weren’t aware of the three sets of eyes that followed yours and Dean’s movement from the side of the room. Sam, John and Bobby talked quietly about Dean’s behaviour, glad to see the young man was laughing and having a good time. Since his break up, he’d been shut off from women emotionally, going back to his old routine of one night stands. Watching how he was with you made the members of his family smile, it had been a long time since Dean looked this happy, his old relationship had worn him down completely and they thought you two looked good together. As long as Dean was happy, that’s all that mattered to them.

“Mind if I cut in?” You both turned to look at Sam, who held a hand out to you, Dean shrugged down at you but you gave him a pleading look that had him smirking.

“She’s all yours brother.” Dean grinned before wondering off, leaving you with Sam.

“He seems happy with you.” Sam told you causing you to blush slightly and immediately try and shut down whatever he was thinking.

“We’re not together. In fact, we haven’t known each other that long and-” Here Sam cut you off, “I don’t think it matters how long you’ve known someone for. I knew Jess for only a few months when I realised that she was it for me. She’s my endgame. I was in high school when I figured that out. If the connection is there then, why deny yourself of what makes you happy. I know I sound like a cliche and it seems I’ve had this love thing figured out, but I don’t, I definitely got lucky with Jessica. Maybe you and Dean are just what each other need right now.”

You looked up at him, eyebrows drawn together. You’d only known Dean for a couple of hours, but what Sam had said about a connection, you felt something with Dean. You could picture yourself dating him, you had a great number of things in common with him, but at the same time you’d literally only met him today.

“Maybe you have a point.” You told him, causing him to grin down at you. He looked over at Dean and noticed his brother’s eyes were still on you, he wondered if they’d ever left.

“Trust me Y/N, I know my brother. He’s into you, but sometimes he won’t do what he wants because he doesn’t want to risk screwing things up. Make a move, I promise it’ll be worth the risk.” Sam smiled at you again, breaking away from you as the song ended. You made your way back to Dean, who grinned when he saw you coming over.

“Hey, are you busy tomorrow?” You asked him, hands fiddling with the bottom of your dress. He smiled and told you he wasn’t, his own hand coming up to run through his hair. “Do you maybe, I don’t know, wanna go out for dinner with me?” He grinned at you.

“On a date?” You nodded, confirming it was indeed a date. “I’d love to go on a date with you Y/N.” With that, he leaned forward and pressed a kiss to your cheek.

**Author's Note:**

> Leave requests in the comments or send me an ask on Tumblr! 
> 
> https://multi-fandom-imagines-x.tumblr.com/post/186361507131/100-prompts-requests-open


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